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Issue 20, 2012
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Synthesis of the unique angular tricyclic chromone structure proposed for aspergillitine, and its relationship with alkaloid TMC-120B

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Abstract

The synthesis of the tricyclic angular chromone structure originally assigned to aspergillitine is reported. The synthesis was achieved in 11 steps and 15% overall yield from 2,4-dihydroxypropiophenone, through the intermediacy of 2,3-dimethyl-7-hydroxychromen-4-one. Construction of the nitrogen-bearing heterocyclic ring entailed a Stille cross-coupling reaction with n-Bu3SnCH2CH[double bond, length as m-dash]CH2, followed by double bond isomerization, oximation of the chromone carbonyl, and a final microwave-assisted electrocyclization of the thus formed 6π-electron aza-triene system.

Graphical abstract: Synthesis of the unique angular tricyclic chromone structure proposed for aspergillitine, and its relationship with alkaloid TMC-120B

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Article information


Submitted
10 Jan 2012
Accepted
19 Mar 2012
First published
19 Mar 2012

Org. Biomol. Chem., 2012,10, 4124-4134
Article type
Paper

Synthesis of the unique angular tricyclic chromone structure proposed for aspergillitine, and its relationship with alkaloid TMC-120B

S. O. Simonetti, E. L. Larghi, A. B. J. Bracca and T. S. Kaufman, Org. Biomol. Chem., 2012, 10, 4124
DOI: 10.1039/C2OB25067E

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